Syntheses and kinetic studies of cyclisation-based self-immolative spacers

被引：17

作者：

Huvelle, Steve ^{[1
]}

Alouane, Ahmed ^{[1
,2
,3
,4
]}

Le Saux, Thomas ^{[2
,3
,4
]}

Jullien, Ludovic ^{[2
,3
,4
]}

Schmidt, Frederic ^{[1
]}

机构：

[1] PSL Res Univ, CNRS, Inst Curie, INSERM,U1143,UMR3666, 26 Rue Ulm, F-75005 Paris, France

[2] UPMC Univ Paris 06, PSL Res Univ, Ecole Normale Super, CNRS,Dept Chim,PASTEUR, 24 Rue Lhomond, F-75005 Paris, France

[3] UPMC, Ecole Normale Super, Dept Chim, CNRS,ENS,PASTEUR24,UMR 8640, 24 Rue Lhomond, F-75231 Paris, France

[4] UPMC Univ Paris 06, Sorbonne Univ, CNRS, ENS,PASTEUR, F-75005 Paris, France

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2017年 / 15卷 / 16期

关键词：

ANTIBODY-DIRECTED ENZYME; TRIMETHYL LOCK; PRODRUG THERAPY; STRATEGIES; RELEASE; ADEPT;

D O I：

10.1039/c7ob00121e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Kinetic analysis of the disassembly of self-immolative spacers based on cyclisation processes was performed. Five compounds were synthesized belonging to two different series, and their kinetic constants were determined. Electron-donating substituents gave a slight acceleration but the main effect was steric, and the Thorpe-Ingold effect was indeed particularly effective. Comparison with the self-immolative spacers based on elimination processes showed that cyclisations gave comparable or lower rate, but the corresponding spacers are more difficult to modulate.

引用

页码：3435 / 3443

页数：9

共 18 条

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Kastrati, Agonist
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Alouane, Ahmed
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Le Saux, Thomas
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Jullien, Ludovic
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (26) : 7492 - 7509
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Alouane, Ahmed
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Le Saux, Thomas
Aujard, Isabelle
Dubruille, Sylvie
Schmidt, Frederic
Jullien, Ludovic
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (35) : 11717 - 11724
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Padula, Daniele
CHEMISTRY-AN ASIAN JOURNAL, 2024, 19 (07)
[5] Design, synthesis, and cyclization of 4-aminobutyric acid derivatives: potential candidates as self-immolative spacers
DeWit, Matthew A.
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ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (06) : 1846 - 1854
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MACROMOLECULES, 2012, 45 (18) : 7364 - 7374
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Roberts, Derrick A.
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CHEMICAL SCIENCE, 2020, 11 (14) : 3713 - 3718
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Dupouy, Christelle
Debart, Francoise
MOLECULES, 2020, 25 (11):
[10] Modular theranostic prodrug based on a FRET-activated self-immolative linker
Redy, Orit
Shabat, Doron
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